Retail Operations Jobs in Chicago, IL (NOW HIRING)

The Role

The Retail Operations Lead is responsible for maintaining the daily operational excellence of the market. This role has primary ownership of receiving, inventory organization, stocking, merchandising, and retail presentation while helping lead the team during daily operations.

Working closely with the Market Manager and Operations Manager, you'll help ensure the market is organized, fully stocked, visually compelling, and ready to deliver an exceptional guest experience every day. While this role is cross-trained in all areas of the business—including register, coffee, and bar service—the primary focus is keeping the retail operation running efficiently behind the scenes and on the sales floor.

• Maintain the overall organization, cleanliness, and presentation of the market throughout each shift.
• Ensure shelves, coolers, displays, and grab-and-go areas remain fully stocked, organized, and guest-ready.
• Monitor product quality, freshness, rotation, and expiration dates.
• Support daily opening and closing procedures and help maintain operational standards across the market.
• Identify operational opportunities and proactively communicate improvements to management.

• Lead the receiving process by checking in deliveries, verifying invoices, inspecting product quality, and organizing backstock.
• Maintain clean, organized, and efficient storage areas that support smooth daily operations.
• Assist with inventory counts, product transfers, and stock replenishment.
• Monitor inventory levels and communicate ordering needs or product shortages to management.
• Help identify inventory discrepancies and work with managers to resolve issues.

• Create an inviting shopping experience through thoughtful merchandising and product presentation.
• Execute seasonal displays, promotional features, merchandising resets, and new product launches.
• Maintain attractive shelves and displays while ensuring products are properly faced, labeled, and rotated.
• Look for opportunities to improve product placement and enhance the guest shopping experience.

• Help set the tone for each shift by communicating priorities, assigning tasks, and leading by example.
• Support and coach team members to maintain hospitality and operational standards.
• Assist with onboarding and training new employees.
• Foster a positive, collaborative, and accountable team environment.
• Serve as a trusted key holder and leader in the absence of a manager.

• Deliver warm, knowledgeable hospitality to every guest.
• Assist guests with product recommendations and market questions.
• Support register, coffee, café, and bar operations during peak business periods or when additional coverage is needed.
• Help fulfill online orders and support guest pickup experiences as needed.

• 2+ years of experience in retail, grocery, specialty food, hospitality, or market operations.
• Previous experience with receiving, inventory management, merchandising, or retail operations strongly preferred.
• Previous leadership, key holder, or supervisor experience preferred.
• Highly organized with exceptional attention to detail.
• Comfortable working in a fast-paced, physically active environment.
• Strong communication and problem-solving skills.
• Passion for food, beverage, retail merchandising, and neighborhood hospitality.

• Ability to lift and move up to 50 pounds and spend extended periods standing, bending, stocking, and organizing.
• Must be at least 21 years old to handle and sell alcohol.
• Ability to safely use box cutters, pallet jacks, dollies, and other retail equipment.
• Comfortable working in refrigerated storage and other varying temperature environments.
• Ability to work a flexible schedule, including evenings, weekends, and select holidays.

Compensation & Benefits

• $18-20 + tips
• 401(k)
• Employee discount on market products, food, and beverages
• Paid sick time
• Paid time off

At Piccadilly Market, we're committed to creating an exceptional neighborhood market experience through hospitality, quality products, and genuine community connection. We're looking for someone who enjoys balancing guest interaction with operational leadership and takes pride in creating an organized, welcoming environment for both guests and teammates.

You'll join a supportive team that values collaboration, hospitality, and continuous learning while gaining hands-on experience in specialty foods, wine, coffee, and market operations. Whether you're looking to grow within the company or deepen your product knowledge, you'll have opportunities to learn, contribute, and make an impact every day.